Manufacture of organic solvents.



HAROLD I-IIIBBERT, or WILMINGTON, DELAWARE, ASSIGNOR To E. I. no roNT 1m NEMOUBS rownnn COMPANY, or WILMINGTON, DELAWARE, A ooRronATIoN OF NEW JERSEY.

MANUFACTURE OF ORGANIC SOLVENTS.

No Drawing.

Specification of Letters Patent.

Patented Feb. 3,1914.

Application filed May 10, 1912. Serial No. 696,342.

To all whom it may concern:

Be it known that I, HAROLD HIBBERT, of

Wilmington, in the county-of Newcastle,

do hereby declare that the following is a,

full, clear, and exact description thereof.

My invention relates to a process for pro ducing condensation products of organic compounds of different kinds, and is applicable to the production of condensation products of many different varieties Within the field of organic compounds comprising compounds belonging to the aliphatic or aromatic series. My invention is particularly applicable, however, to the produc; tion of condensation products of aldehydes and ketones. My invention. is especially adapted to the production of acetaldol from acetaldehyde by the condensation of two molecules of acetaldehyde to produce one molecule of acetaldol, in accordance with the following equation Prior to the time of my invention, such condensation products have been obtained by the use of different substances, preferably,

' small, and further, that the isolation of .the

condensation products from aqueous solutions is tedious and expensive. -The metallic hydroxids could not be used for this purpose as their addition to acetaldehyde has resulted in producing yellow resinous products, known as acetaldehyde resins. (See the Lehrbuch der Organz'sche-n Ohemz'e of Meyer-Jacobson.) I have discovered that this action of metallic hydroxids in producing such resinous products is especially marked in the presence of water. By means of my invention, in which I effect the condensation in solvents other than water, I am enabled to obtain condensation products by the use of metallic hydroxids such, for ex ample, as potassium or sodium hydroxid without any tendency whatever to produce the resinous products ordinarily obtained by the action of metallic hydroxids in aqueous and other solutions.

Incarrying out my invention I cause the action of the hydroxid to take place in a solution of the carbon compound acted upon in a non-aqueous liquid. I preferably use for this purpose a light hydrocarbon liquid such as gasolene, but I may use for this purpose any other anhydrous liquid which will dissolve the carbon compound to be acted upon without reacting with the same.

While my invention is capable ofapplication to many different condensation reactions, as one illustrative embodiment thereof I may proceed as follows: I dissolve a quantity of acetaldehyde having a boiling point of 21 to 28 C., in a hydrocarbon or mixture of hydrocarbons such as gasolene. This solution is then cooled to the temperature of. substantially -10 C. I then suspend in the liquid a small piece of solid caustic potash'or caustic soda. In a few moments a condensation of the acetaldohyde'takes place, acetaldol being formed on the surface thereof. The acetaldol thus formed bein insoluble in the hydrocarbon solvent and aving a higher specific gravity than the solution, separates out and accumue lates' at the bottom of the vessel. This action ofthemetallic hydroxid is effected without the production of any appreciable higher condensation products.v When the action is completed, the immiscible liquids may be separated and any unchanged acetaldehyde, together with any gasolene -rerated therefrom by distillation, the latter being obtained as a clean-colorless product having a, sharp boiling point between and C., under'a pressure of 20 mm. Not only may this action be effected by the use of other carbon compounds and other anhythe use of these latter substancesis not ad vantageous, owing to the small degree of yield obtained and the slowness of the action.

By condensation I mean the union of molecules to produce a compound from .90 maining with the acetaldol may be sepawhich the original substance or substances cannot be regenerated byany simple method.

While I have described my invention 'in a substantially anhydrous liquid, a solid substance capable of -producin'g a condensation product of the carbon compoumhthe actlon being effected between like molecules of the carbon compound without the splitting off of atoms from'any' of the compounds in contact with said substance.

2. The process which comprises forming a condensation product.- by bringing into contact with an aldehyde dissolved in a sub-' stantially anhydrous liquid, a solid substance capable of producing a condensation product of the aldehyde, the action being efi'ected between like molecules of the carbon compound without the splitting off of atoms from any of thecompoundsin contact with said substance.

3.v The, process which comprises forming a condensation product by bringing into contact with an aldehyde dissolved in a substantially anhydrous liquid, a solid metallic hydroxid, the action being e-fi'ected between like molecules of the carbon compound without the splitting oil of atoms. 4.. The process which comprises forming a condensation product by bringing into contact with a carbon compound dissolved in a substantially anhydrous liquid in which the condensation product is insoluble, a sub-- stance capable of producing a condensation product of the carbon compound, the action being efi'ected between like molecules of the carbon compound without the splitting ofl' of atoms. v

5. The process which comprises forming a condensation product by bringing into. contact with analdehyde dissolved in a substantially anhydrous liquid in which thev condensation product is insoluble, a substance capable of producing a condensation product of the aldehyde.

6. The process which comprises forming a condensation product by bringing into contact with a carbon compound dissolved in a substantially anhydrous liquid in which the condensation product is insoluble, a men tallic hydroxid, the action being effected between like molecules of the carbon compound without the splitting ofi' of atoms.

7. The process which comprises forming a condensation product by bringing into accepts contact with an aldehyde dissolved in a substantially anhydrous liquid in which the carbon compound without the splitting 01f ofatoms and then drawing oil the separated condensation'product thus produced.

9. The process which comprises forming a: condensation product by bringing into contact with an'aldehyde dissolved in a substantially anhydrous liquid in which the condensation product is insoluble, a substance. capable of producing a condensation product of the aldehyde, and then drawing oft the separated condensation product thus produced.

10. The process which comprises forming a condensation product by bringing into contact with a carbon compound dissolved in a substantially anhydrous liquid in which the condensation product is insoluble, a metallic hydroxid, the action being efl'ected between like molecules of the carbon compound without the splitting off of atoms, and then drawing off the separated condensation product thus produced.

11. The process which-comprises forming a condensation product by bringing into contact with an'aldehyde dissolved in a substantially anhydrous liquid in which the condensation product is insoluble, a metallic hydroxid, and then drawing oil the separated condensation product thus produced;

12." The process of producing acetaldol comprising subjecting a solution of acetaldehyde in gasolene to the action of a caustic alkali; q

13. The process of producing acetaldol comprising subjecting a solution of acetaldehyde in gasolene to the action of potassium hydroxid.

14. The process which comprises forming a condensation product by bringing into contact with a carbon compound dissolved in a substantially anhydrous liquid, a solid metallic hydroxid, the action being effected between like molecules of the carbon compound without the splitting off of atoms.

In testimony that I claim the foregoing I have hereunto set my hand.

HAROLD HIBBERT.

Witnesses:

C, R. MUDGE, A. M. GORMAN. 

